Open Letters

While my time working directly with you at Zappos was brief, I learned a good deal about great leadership and about myself. This letter is a reflection on some of those things.

I was tasked with heading up the team + strategy for the first mobile apps at Zappos in June of 2010. My first meeting on the project was listening to a room full of people who’d been working on a version of the product for several months prior. Upon completion of that meeting, I was approached by several individuals who each said something along the lines of, “I know we just discussed that, but Tony really wants this.” And each person had a completely different version of what “Tony wants.” Which led me to ask my boss at the time, “Can I just ask Tony what Tony wants?”

The three of us sat down, I asked you a handful of UX-ey/vision/business objective questions, you answered each with direct simplicity. I walked out of that meeting feeling like I knew exactly what we needed to do, without having been given any specific directive on how to do it. In summary, your most defining point was, “I just want something I’m not embarrassed to Tweet about.” Of course there was more to it than that, but that line sums up the fact that you communicated a very clear business objective and trusted us — the team tasked with pulling it off — to deliver something that exceeded expectation. And we did. Eight weeks later we went from having never touched an iPad to having the first iPad app for Zappos, raining cats to boot. Our team worked really hard and had a lot of fun. Lesson learned: Great leaders trust they’ve made great hiring decisions, communicate clear objectives, then get out of the way.

I know I’ve not always been the easiest person to be a manager of. About 85% of my job history (the patches where I’ve been an employee as opposed to self-employed) is made up of roles that didn’t exist before I held them. Those roles were open for me to define and grow as I saw fit as long as the activities of the role supported business objectives. My role at Zappos started out that way and I did some my best work under those conditions. Two of the four managers I had during my two-year tenure at Zappos were really amazing people who understood how to work with someone like me. I learned a lot and I’m grateful for it all. Lesson learned: Great hiring is about finding a person with great ecology to bring to a team, not finding a round peg that must fit into a round hole. Great leaders know how to fuel someone who has the right team ecology.

You had my back when I felt passionate about something, whether I was right, or just being passionate was never in question. You trusted that my passion came from the right place, and trusted that my reasons were sound. While I’ll not point out the specific example, I believe to this day we made the right decision. You put my care/concern for quality over checking off a box on the roadmap. Lesson Learned: Great leaders ask and listen to how much their people care about something before making an “executive decision.” Whether that decision results in success or failure, everyone learns a lot from the process.

A couple years ago I invited you to be on a podcast I was co-hosting. You were kind enough to accept the invitation, we scheduled, and somehow I ended up with the wrong date in my calendar, and as it turned out I was going through security at an airport at the exact moment you emailed to find out if we were still doing the show. I’ve never been more embarrassed for wasting someone’s time as I was in that moment. I still feel bad about it because I value time as a precious commodity. Wasting yours, mine or anyone else’s is not a thing I want any part of. I know I apologized for it already, but ya. Ugh. Lesson Learned: Don’t waste people’s time. Be succinct, be clear, be mindful, be organized. Get better at using a calendar and write more stuff down.

I’ll keep it at that for now. Thanks again for all you do, and all you’ve done. It was an honor to have worked with and learned from you.